Al(OTf)<sub>3</sub>-Catalyzed Regioselective N<sup>2</sup>–Arylation of Tetrazoles with Diazo Compounds
Shuqi Zhou, Chunyan Li, Jie Zeng, Jian Lv, Jie Liao, Haifeng Wang, Qiongjiao Yan, Shuang‐Xi Gu
Abstract
Regioselective methods to access alkylated tetrazoles still remain a challenging goal. Herein, we describe a novel regioselective protocol for N 2 -arylation of tetrazoles with diazo compounds using inexpensive Al(OTf) 3 . This reaction could be conducted under mild conditions to access a diverse array of alkylated tetrazoles with 2-substituted tetrazoles as the major products, demonstrating a comprehensive range of substrate compatibility and excellent functional group compatibility. Mechanistic studies revealed a carbene-free process in this reaction procedure. Furthermore, the scale-up reaction and transformations of the N 2 -arylation of tetrazole products demonstrated the potential of this strategy.